Triethylamine → t-Butyl-4-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate

HRID 384845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384845
Cl.C(N=C=NCCCN(C)C)C.Cl.[CH2:14]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][C:23]=1[O:30][CH3:31])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH:42]([C:45](O)=[O:46])[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].C(N(CC)CC)C>C(Cl)Cl>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH:42]([C:45](=[O:46])[NH:27][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:23]([O:30][CH3:31])[CH:24]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162477591-[4-(Benzyloxy)-3-methoxyphenyl]methanamine--hydrogen chloride (1/1)

Produkt 1

HCID 66587122t-Butyl-4-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylateAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (12.5 g) was added to a mixture of 4-benzyloxy-3-methoxy benzylamine hydrochloride (14.0 g), 1-(t-butoxycarbonyl)-piperidine-4-carboxylic acid (11.5 g), triethylamine (14.0 ml) and methylene chloride (300 ml). After stirring the reaction mixture at room temperature for 20 hours, the mixture was washed with saturated ammonium chloride aqueous solution and then saturated brine, the organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient) to obtain 16.3 g of t-butyl-4-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate.

Aufarbeitung

  1. washthe mixture was washed with saturated ammonium chloride aqueous solution
  2. dry with materialsaturated brine, the organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-905b62f0ad214204980c60768b785b3a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367835B2

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